#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/30/2013032.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2013032
loop_
_publ_author_name
'Meszko, Joanna'
'Sikorski, Artur'
'Huta, Olexyj M.'
'Konitz, Antoni'
'Błażejowski, Jerzy'
_publ_section_title
;
 10-Methyl- and 9,10-dimethylacridinium methyl sulfate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o669
_journal_page_last               o671
_journal_paper_doi               10.1107/S0108270102017171
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C14 H12 N + , C H3 O4 S -'
_chemical_formula_sum            'C15 H15 N O4 S'
_chemical_formula_weight         305.34
_chemical_name_systematic
;
10-methylacridinium methyl sulfate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 115.23(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.199(5)
_cell_length_b                   12.661(4)
_cell_length_c                   14.785(4)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.0
_cell_measurement_theta_min      6.0
_cell_volume                     2743.1(16)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma Diffraction, 1989)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2774
_diffrn_reflns_theta_full        71.99
_diffrn_reflns_theta_max         71.99
_diffrn_reflns_theta_min         4.62
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.251
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.54
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1082P)²+1.7878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.147
_refine_ls_wR_factor_ref         0.168
_reflns_number_gt                2150
_reflns_number_total             2663
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1138.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2013032
_cod_database_fobs_code          2013032
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.26367(4) 0.46170(5) 0.10441(4) 0.0419(3) Uani d . 1 . . S
O1 0.32483(14) 0.44867(16) 0.04407(15) 0.0540(5) Uani d . 1 . . O
O2 0.23487(15) 0.56980(16) 0.08212(17) 0.0631(6) Uani d . 1 . . O
O3 0.32312(16) 0.44171(18) 0.20691(15) 0.0604(6) Uani d . 1 . . O
O4 0.19128(15) 0.38575(18) 0.06352(18) 0.0667(6) Uani d . 1 . . O
C1 -0.06295(19) 0.2587(2) 0.0532(2) 0.0533(7) Uani d . 1 . . C
H1A -0.1163 0.2811 0.0002 0.064 Uiso calc R 1 . . H
C2 -0.0459(2) 0.1544(3) 0.0698(2) 0.0634(8) Uani d . 1 . . C
H2A -0.0875 0.1051 0.0287 0.076 Uiso calc R 1 . . H
C3 0.0355(2) 0.1207(2) 0.1498(2) 0.0628(8) Uani d . 1 . . C
H3A 0.0468 0.0487 0.1603 0.075 Uiso calc R 1 . . H
C4 0.0979(2) 0.1902(2) 0.2120(2) 0.0540(7) Uani d . 1 . . C
H4A 0.1511 0.1656 0.2640 0.065 Uiso calc R 1 . . H
C5 0.1889(2) 0.5553(2) 0.3026(2) 0.0529(7) Uani d . 1 . . C
H5A 0.2421 0.5336 0.3563 0.063 Uiso calc R 1 . . H
C6 0.1715(2) 0.6606(3) 0.2830(2) 0.0594(7) Uani d . 1 . . C
H6A 0.2138 0.7098 0.3233 0.071 Uiso calc R 1 . . H
C7 0.0914(2) 0.6962(2) 0.2038(2) 0.0590(7) Uani d . 1 . . C
H7A 0.0809 0.7682 0.1925 0.071 Uiso calc R 1 . . H
C8 0.02934(19) 0.6259(2) 0.1437(2) 0.0510(6) Uani d . 1 . . C
H8A -0.0238 0.6497 0.0912 0.061 Uiso calc R 1 . . H
C9 -0.01673(17) 0.4416(2) 0.09988(19) 0.0460(6) Uani d . 1 . . C
H9A -0.0704 0.4641 0.0474 0.055 Uiso calc R 1 . . H
N10 0.14120(14) 0.37353(18) 0.25871(15) 0.0425(5) Uani d . 1 . . N
C11 0.00023(16) 0.3344(2) 0.11630(18) 0.0436(6) Uani d . 1 . . C
C12 0.08175(17) 0.2998(2) 0.19731(19) 0.0437(6) Uani d . 1 . . C
C13 0.04510(17) 0.5160(2) 0.16049(19) 0.0435(6) Uani d . 1 . . C
C14 0.12617(17) 0.4800(2) 0.24143(18) 0.0432(6) Uani d . 1 . . C
C15 0.22459(18) 0.3402(3) 0.3454(2) 0.0562(7) Uani d . 1 . . C
H15C 0.2247 0.2647 0.3519 0.084 Uiso calc R 1 . . H
H15B 0.2263 0.3724 0.4050 0.084 Uiso calc R 1 . . H
H15A 0.2772 0.3617 0.3360 0.084 Uiso calc R 1 . . H
C16 0.3738(3) 0.3523(3) 0.0578(3) 0.0715(9) Uani d . 1 . . C
H16C 0.4022 0.3498 0.0126 0.107 Uiso calc R 1 . . H
H16B 0.3326 0.2939 0.0447 0.107 Uiso calc R 1 . . H
H16A 0.4199 0.3483 0.1254 0.107 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O3 S1 O4 112.83(15) ?
O3 S1 O2 114.68(13) yes
O4 S1 O2 114.46(14) yes
O3 S1 O1 105.99(13) ?
O4 S1 O1 106.56(12) ?
O2 S1 O1 100.83(12) yes
C16 O1 S1 116.73(18) ?
C2 C1 C11 120.4(3) ?
C2 C1 H1A 119.8 ?
C11 C1 H1A 119.8 ?
C1 C2 C3 119.6(3) ?
C1 C2 H2A 120.2 ?
C3 C2 H2A 120.2 ?
C4 C3 C2 122.0(3) ?
C4 C3 H3A 119.0 ?
C2 C3 H3A 119.0 ?
C3 C4 C12 119.8(3) ?
C3 C4 H4A 120.1 ?
C12 C4 H4A 120.1 ?
C6 C5 C14 119.8(3) ?
C6 C5 H5A 120.1 ?
C14 C5 H5A 120.1 ?
C5 C6 C7 121.6(3) ?
C5 C6 H6A 119.2 ?
C7 C6 H6A 119.2 ?
C8 C7 C6 120.1(3) ?
C8 C7 H7A 119.9 ?
C6 C7 H7A 119.9 ?
C7 C8 C13 120.2(3) ?
C7 C8 H8A 119.9 ?
C13 C8 H8A 119.9 ?
C11 C9 C13 121.1(2) ?
C11 C9 H9A 119.4 ?
C13 C9 H9A 119.4 ?
C12 N10 C14 121.7(2) yes
C12 N10 C15 120.4(2) yes
C14 N10 C15 117.8(2) ?
C9 C11 C12 119.5(2) ?
C9 C11 C1 120.8(2) ?
C12 C11 C1 119.7(3) ?
N10 C12 C4 122.4(2) ?
N10 C12 C11 119.1(2) ?
C4 C12 C11 118.5(2) ?
C9 C13 C8 121.7(2) ?
C9 C13 C14 118.6(2) ?
C8 C13 C14 119.6(3) ?
N10 C14 C5 121.6(2) ?
N10 C14 C13 119.8(2) ?
C5 C14 C13 118.6(3) ?
N10 C15 H15C 109.5 ?
N10 C15 H15B 109.5 ?
H15C C15 H15B 109.5 ?
N10 C15 H15A 109.5 ?
H15C C15 H15A 109.5 ?
H15B C15 H15A 109.5 ?
O1 C16 H16C 109.5 ?
O1 C16 H16B 109.5 ?
H16C C16 H16B 109.5 ?
O1 C16 H16A 109.5 ?
H16C C16 H16A 109.5 ?
H16B C16 H16A 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.599(2) yes
S1 O2 . 1.438(2) yes
S1 O3 . 1.430(2) yes
S1 O4 . 1.436(2) yes
O1 C16 . 1.422(4) yes
C1 C2 . 1.350(4) ?
C1 C11 . 1.422(4) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.411(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.360(4) ?
C3 H3A . 0.9300 ?
C4 C12 . 1.412(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.368(4) ?
C5 C14 . 1.406(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.400(4) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.354(4) ?
C7 H7A . 0.9300 ?
C8 C13 . 1.417(4) ?
C8 H8A . 0.9300 ?
C9 C11 . 1.385(4) ?
C9 C13 . 1.389(4) ?
C9 H9A . 0.9300 ?
N10 C12 . 1.370(3) ?
N10 C14 . 1.375(3) ?
N10 C15 . 1.473(3) yes
C11 C12 . 1.422(3) ?
C13 C14 . 1.423(3) ?
C15 H15C . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15A . 0.9600 ?
C16 H16C . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16A . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1A O2 1_555 1_555 3_565 0.93 2.60 3.424(4) 149 yes
C2 H2A O1 1_555 1_555 5_445 0.93 2.50 3.261(4) 139 yes
C3 H3A O3 1_555 1_555 6_545 0.93 2.57 3.276(4) 133 yes
C4 H4A O2 1_555 1_555 6_545 0.93 2.54 3.449(4) 164 yes
C5 H5A O1 1_555 1_555 4_565 0.93 2.52 3.300(4) 141 yes
C9 H9A O2 1_555 1_555 3_565 0.93 2.57 3.412(4) 151 yes
C15 H15A O3 1_555 1_555 1_555 0.96 2.53 3.344(4) 141 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O3 S1 O1 C16 53.6(3) ?
O4 S1 O1 C16 -66.9(3) ?
O2 S1 O1 C16 173.4(2) yes
C11 C1 C2 C3 -0.5(5) ?
C1 C2 C3 C4 0.4(5) ?
C2 C3 C4 C12 0.2(5) ?
C14 C5 C6 C7 1.0(5) ?
C5 C6 C7 C8 -0.7(5) ?
C6 C7 C8 C13 -0.1(4) ?
C13 C9 C11 C12 0.8(4) ?
C13 C9 C11 C1 -179.3(2) ?
C2 C1 C11 C9 -180.0(3) ?
C2 C1 C11 C12 0.0(4) ?
C14 N10 C12 C4 177.6(2) ?
C15 N10 C12 C4 -1.6(4) ?
C14 N10 C12 C11 -3.0(3) ?
C15 N10 C12 C11 177.8(2) yes
C3 C4 C12 N10 178.6(3) ?
C3 C4 C12 C11 -0.7(4) ?
C9 C11 C12 N10 1.2(4) ?
C1 C11 C12 N10 -178.7(2) ?
C9 C11 C12 C4 -179.4(2) ?
C1 C11 C12 C4 0.7(4) ?
C11 C9 C13 C8 179.0(2) ?
C11 C9 C13 C14 -1.0(4) yes
C7 C8 C13 C9 -179.5(3) ?
C7 C8 C13 C14 0.5(4) ?
C12 N10 C14 C5 -177.8(2) ?
C15 N10 C14 C5 1.4(4) ?
C12 N10 C14 C13 2.8(4) yes
C15 N10 C14 C13 -177.9(2) ?
C6 C5 C14 N10 -180.0(3) ?
C6 C5 C14 C13 -0.6(4) ?
C9 C13 C14 N10 -0.7(4) ?
C8 C13 C14 N10 179.2(2) ?
C9 C13 C14 C5 179.8(2) ?
C8 C13 C14 C5 -0.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11488632
